Triethyl orthoacetate → 3-(3-chloro-4-(dihexylamino)phenyl)-2,6-dimethylpyrimidin-4(3H)-one

HRID 56200Notes

Reaction equation

[NH2:1]/[C:2](/[CH3:27])=[CH:3]\[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:9]([Cl:26])[CH:8]=1)=[O:5].[C:28](OCC)(OCC)(OCC)[CH3:29]>>[Cl:26][C:9]1[CH:8]=[C:7]([N:6]2[C:4](=[O:5])[CH:3]=[C:2]([CH3:27])[N:1]=[C:28]2[CH3:29])[CH:12]=[CH:11][C:10]=1[N:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

Reactant 2

HCID 66221Triethyl orthoacetate

HCID 90022952(Z)-3-amino-N-(3-chloro-4-(dihexylamino)phenyl)but-2-enamide

Product 1

HCID 729501773-(3-chloro-4-(dihexylamino)phenyl)-2,6-dimethylpyrimidin-4(3H)-oneYield 33%

Conditions

Temperature: 150 °C

Procedure

A mixture of (Z)-3-amino-N-(3-chloro-4-(dihexylamino)phenyl)but-2-enamide (3.94 g, 10 mmol) and triethyl orthoacetate (80 mL) was stirred at 150° C. overnight. The mixture was then cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as pale yellow oil (1.36 g, 33%). The compound was characterized by the following spectroscopic data:

Workup

temperatureThe mixture was then cooled to rt
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

Sources & evidence

ORD record: ord-2c2c2c1f8e914ab88cf1bb02af7ba1c7
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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